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I was never very good at talking to girls, especially pretty ones I was interested in, when I was young. I think it had something to do with the constant bullying I took throughout highschool. I was an easy target being a skinny (105lbs when I graduated), scrawny (could barely bench 80lbs), with long blonde hair (at the time, I thought it was cool…but looking back it was terrible and I was constantly mistaken for a girl), and I had pastey white skin. What made it worse was that I hadn’t a single hair on my body at age 19. I looked much younger than I actually was. I had only one friend from school…Tina. We both grew up in the same trailer park and if it wasn’t for her, I’m not sure I would of survived highschool. It took me till I was 19 to finally confess my feelings to Tina. What I didn’t know was, that she had known for years and our relationship was about to change.
Tina was one of those girls who “matured” quickly. She was the first girl in school that had to wear a bra. I can’t tell you how many times I thought of her breasts as I masturbated. She always wore low cut shirts and wasn’t afraid to show off cleavage. Tina was a thick curvy girl. She was about as wide as she was tall 5’4″ to be exact. Tina always had long brown hair she wore in ponytails. She was very loud compared to me being so quiet. She had a mouth on her and I wished I could speak my mind like she did. Tina dated lots of guys but she always would let me hang out with her. It killed me when she’d tell her boyfriend’s that I was like a “brother” to her and when she told me of her sexual exploits. I would imagine myself in them while masturbating all the time.
Fast forward to the summer after my freshman year at college. I had been away from the small town I had grown up in. My complexion had cleared and I was finally confident to tell Tina how I felt about her. I was excited to see her and catch up. But I was sidelined, Tina had gotten engaged! Tina had stayed back in our home town while I left the state to attend college. We had talked on the phone to each other for the first month but I stopped calling her back after making friends and meeting a girl. Tina didn’t take the news well and her attitude changed towards me which left me confused. Still, Tina haunted my mind… I found myself masturbating while thinking about her. I couldn’t stop myself. It led to the dissolution of my first relationship with a girl. I decided I had to tell Tina how I felt!
I had been back for two days when I heard about Tina’s engagement. I was initially shocked but decided I had to tell her. Instead of calling, I drove out to the house she was living at with her fiance. I knew the guy she was engaged to and also knew he wasn’t going to be home since he worked the second shift at a manufacturing plant. I pulled up and there Tina was. She was mowing the grass on a riding mower. Tina had on shorts and bikini top. She had gained weight but still looked sexy to me. She saw my car and waved me over to the barn. I got out and before I said a word Tina asked “Where’s your girlfriend?” In a mocking tone. She had derailed the speech I had been planning in my head for weeks in just a few seconds. I stammered out a sad story of how she left me for someone else. Tina smirked, almost broke out laughing. Her body was covered in sweat, her long brown hair was caked to her body, I found myself staring at her tan chest, and the tanlines from her bikini showing off small bits of pale skin. I felt my penis harden in my shorts. Tina knew I was staring. She shook her head. Smiled and walked up to me and hugged me tight. Her sweaty body pressed up against me. My cock swelled. She looked up at me with her dark brown eyes. “Want to fuck?”
I nearly fell over. My legs got weak. My hearbeat was racing. I couldn’t respond. Tina broke out laughing. “I figured you came here to get laid. You’re still a virgin, right??” I awoke to reality. Tina was just teasing….or was she? I figured she probably was as she walked away up to the house. I followed instinctively behind looking at her hips move and ass shook as she strutted ahead of me. I finally spoke confessing that I was no longer a virgin. Tina turned around, “Well, good for you.” She gave a golf clap. I felt embarrassed and my cheeks went flush. I’m sure she thought it was with my ex girlfriend but she couldn’t of been more wrong in that moment. I got angry with myself and how Tina was mocking me. I considered leaving for a brief second. My anger fueled me to catch up to Tina just before she opened her screen door. I grabbed her arm, turned her around and said “I have been afraid to tell you this but not anymore”, my whole body got a warm sensation,” I have strong feelings for you!” Tina wasn’t even surprised! She smiled and said “I always knew” She jerked free of my grip and headed inside. “Want something to drink?”
I followed in quietly into the kitchen. She got two glasses out and filled them with water from the sink. Tina handed me one. As I drank, “I always knew you had a crush on me and I had hoped you would of done something about it”, she sat down in a chair by the kitchen table. “But you never did anything, I assumed you were gay!” A thought ran in my mind… I wanted to rip my clothes off and take her there on the kitchen table…. I got lost in that thought for a few seconds. Tina cleared her throat”Hello!?!” I then confessed about me masturbating while looking at pictures of her and thinking about her. I opened up about the sex she had with her previous boyfriends and how I wished it had been me. I could help but stare at her enormous breasts in that bikini top. I was so hard and I knew she could see the buldge sticking out towards her in my shorts. Then Tina took a long drink, slamming the glass on the table. She leaned back, stretched her arms behind her head, stuck out her chest and stomach, spread her legs apart and in a surprisingly cold tone ” well, let’s see you masturbate.”
I’m unsure if it was the challenge or my willingness to be naked in front of her. I took my shirt off, unzipped my shorts and pulled them down around my ankles. I started to rub myself in Tina’s kitchen but she raised a hand to stop me. My tiny thick cut cock bounced up and down pointing directly at her. Tina stood up and walked up to me. She put a hand on it and softly closed her hand around it. I shivered at her touch. I couldn’t be she held my rod in her hands. The thought passed quickly as she tightened her grip and jerked hard on me. I’m sure the painfully confused look was met with Tina’s intense look. “Follow me!” She held my cock firmly, turning me around and up the stairs. She let my throbbing cock go. Tina looked into my longing eyes. She untied her bikini top and unveiled the most magnificent tits I’ve ever seen. Small pale triangular shapes surrounded her puffy erect nipples. Her breasts fell down to round belly. She slipped out of her shorts and panties to reveal her completely bare pussy. Tina came over and rubbed my body. “I like no body hair” She pressed her fleshy body up against mine. Her sweaty body melted me. I felt weak and warm. She walked behind me and pressed her breasts up against my backside. She reached around and began jerking me off in front of a large mirror. She stared at me from behind as I reached back for her. Tina stare was dark and she got this evil grin on her face as she touched me. “I bet you like from behind.” Just the way she said it made my whole body shiver. “I imagined that tight little ass of your filled with cock” Tina slyly spoke into my ear. Just then she shoved a finger up into my ass. I jumped, then my body jerked as cum squirted out onto the mirror. A mixture of emotions flooded me , I was angry for cumming already, I was mad at how weak I felt in this moment, I felt relief that she somehow knew about my virginity lost to a 37year old man I barely knew, I felt extacy as the cum was extracted by her second finger now jammed up inside me continuing to finger fuck me. The cum had escaped through me tip and now drained out over Tina’s hand. She continued to work in a third finger up inside me from behind. I fell forward and struggled to stand against the dresser in front of the mirror. Tina looked pleased by my weakness. She pulled her fingers out and released my cock from her talons. I didn’t realize how hard she was gripping me. A strong wave of pain crippled me and I fell down to me knees. Tina walked over to a closet and disappeared into it. “Get on the bed!” Tina ordered.
I collapsed onto the bed. Tina commanded that I lean over the bed and face the mirror. She walked out wearing a strap on. It was a large long black cock. She was rubbing lube on it. “I want you to watch me fuck your brains out!” Tina wasn’t smiling any more. “I’m going to give it to you just like I do to my fiance.” I reached forward on the bed gripped the mattress as tight as I could. Tina kicked apart my legs. She pried my cheeks apart and pulled my hole apart. She spit down into me. I was grossed out by it amazingly. Instead it was a curiosity of what was about to happen next is what kept me doing what Tina told me to do. She thrusted the thick rubbery cylindrical shaft into my backside. My legs quivered and shook as she drilled deeper into me. I felt like it was traveling up my throat the deeper she pressed. “Say his name!” Tina shouted. I called out “Mike! Mike!” Tina pounded deeper. I felt my hole being enlongated . My stomach began to extend outward from the penetration. The curiosity sensation became one of pain. I no longer wanted any more. Tina began panting, shouted out “You’re mine you gay bitch!” My head was bobbing up and down my neck ached along with my entire body. Tina dove in as deep as she could burying her strap on completely inside me. I began to cry out “I’m done! No more! Please stop!” My one leg curls up and was shaking badly. It was cramping up. I tried to pull away but Tina’s weight pinned me down as she wiggled a little deeper. Her sweaty body was matched by mine. I bit down on the covers and screamed as loud as I could into them. “If you want it out, push it!” Tina unharnessed the device and pressed down on my cheeks as she spread them. I pushed hard. I made juicy fart noises as is finally slid slowly out of me. With a loud gasp I pushed it all the way out. It hit the floor with a loud thud. I pulled myself up on the bed into a ball position. Tina sat next to me and ran her fingers through my sweaty hair. I looked up at her curvy body into her eyes. She smiled and seemed like she wanted to say something but held back. Tina let me recover for a few minutes longer before rolling me onto my back. She moved her thick thighs around my head and forced me to lick her as she tortured me with suffocation. I almost blacked out two times as I performed oral. Three hours later I was sent home with further instructions…
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